John Shedden studied at the Irvine Academy in Irvine, Ayrshire, and worked on the Glasgow and South Western Railway before emigrating to Virginia in the United States where he became a railway contractor. In 1855 he came to Canada and entered into a partnership with William Hendrie of Hamilton to form the cartage firm of Hendrie and Shedden. They were the cartage agents for the Great Western Railway and later became the agents for the Grand Trunk after its line from Montreal to Toronto was completed in late 1856. The firm introduced in Canada some of the features of cartage firms in England, such as making facilities available in several cities (in 1857 the firm had offices in Toronto, Hamilton, and London), and it improved on the service previously provided by cartage firms in Canada. It employed heavier wagons and standardized the more important forms used by the railways in moving freight. Nonetheless, the monopoly position of the firm inevitably led to complaints. A riot is said to have occurred in Montreal after meetings held to protest this monopoly, and the firm’s barns were burned on two occasions.

Hendrie and Shedden dissolved their partnership in 1859 or 1860, and the latter retained the contract with the Grand Trunk. He continued to expand his company’s facilities, and by 1870 he had offices in Montreal, Toronto, London, and Detroit, and owned about 400 horses. He was, however, developing other interests, particularly as a contractor and as a railway promoter.

Shedden became associated with a group of prominent Toronto businessmen, including George Laidlaw* and J. G. Worts*, who were actively promoting the construction to the areas north of Toronto of narrow-gauge railways which, it was believed, could be built more cheaply and quickly than railways with a wider gauge. Shedden had already been a contractor for several buildings in Toronto, including the Grand Trunk grain elevator, opened in 1863, and Union Station, completed in July 1873. He now became a railway contractor, in partnership with William James Mackenzie, on the narrow-gauge Toronto, Grey, and Bruce Railway, chartered in 1868 and completed from Toronto to Owen Sound in June 1873. He was also an important stockholder in the railway, and in 1870 became a director. Another narrow-gauge railway was the Toronto and Nipissing, completed as far as Coboconk in November 1872. Shedden was elected its president in 1870 and was an important stock and bondholder in the company.

Shedden did not participate actively in politics but he had close associations with the Conservative party and Sir John A. Macdonald*. He had been a director of the Toronto Daily Telegraph (and probably lost some money when it was discontinued in 1872), and he and C. J. Campbell signed in 1872 a note for $10,000 to Macdonald “to enable him to supply funds to the several constituencies which he hopes to carry.” He had been included in 1872 in the Interoceanic Railway Company headed by David Lewis Macpherson*, which Macdonald failed to amalgamate with Sir Hugh Allan*’s Canada Pacific Railway Company. Macdonald then tried to persuade Shedden to enter a company that was being formed. Shedden was disappointed in not receiving the vice-presidency of the company and, although he “could have managed the financial part of it,” he refused Macdonald’s offer at the last moment because of an unspecified “difficulty.”

Shedden was included in the provisional board of directors of the St Lawrence Bank in 1872, and he was a director in a number of other firms. He died as a result of an accident at Cannington on 16 May 1873 when he was crushed between moving cars on the Toronto and Nipissing Railway line and the station platform.

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